Anal play is the most requested practice my subs ask for and I think for many other Mistresses too, as well as being extremely humiliating and emasculating, a lot of men are finally discovering their "P-spot" and exploring the joys of prostate stimulation.
There is a lot of strap on based porn out there, thousands (dare I say many more...?) of men have been enjoying it in the UK for years and thousands more are thinking about/starting to do it, but while it's easy to be excited by a porno showing some poor strapped up sub getting double hand fisted or fucked with the mother of all monster dildo's, being able to do that yourself as a newb to it all is not going to happen over night and it's important to know what to expect and what your body is capable of. If you turn up to your first session all over enthused begging Mistress to shove her biggest cock up your arse you're going to leave sorely disappointed instead of sorely bum fucked, because you've got eyes bigger then your arseholes!
You may have heard of the term 'Anal Training' and it exists for a reason, getting to a point where you can take more than a finger is a process, a commitment even!
So here's what you need to know about getting into anal play -
Wanting to explore it does not make you gay!
If you are physically and sexually attracted to men then it sounds like you could be at the very least bisexual, but the act of receiving anal pleasure isn't "gay", anal play does not belong to homosexual men it's just the only hole they have available to play with. If you desire to serve a stunning dominating woman, who is so hot in her stockings and heels that you'll even let her fuck you in the ass then I think it's safe to say you're straight! Italians even have a term for it "morto di figa" refers to a man who is willing to " die for pussy!" and those Italian guys are ALL filthy bastards.
The reality is you guys have a very pleasurable spot up there and you all should see what that shit's about, feminists are always talking about how important their clit and G-spots are, your bits are just as important!
You have a pleasure button, science says so, so make the most of it or what would be the point of having it!?
Before you can enjoy it, you have to get used to the feeling of something going in instead of out!
Feeling like you're shitting backwards takes a little minute to get your head around, it will be uncomfortable, only slightly painful if at all, but mostly awkward. You need to remember to relax, breath and use lots of lube! I always recommend that you at least spend some time fingering yourself before you decide to let someone else get in there, it's always preferable to deal with the shock of it all in private rather than in the company of the very first professional you chose to visit! Get comfortable with some degree of activity down there and with yourself!
The anus is a muscle and it needs to be trained. Properly!
It's a very tight muscle and for damn good reason! So just as you have to gently stretch your muscles at the gym for improved flexibility, the same works with your ass. I seeing you eyeing up that 16 inch black bad boy but you can forget about it bitch, that right there is running before you can even crawl!
The sphincter muscle will have to to be stretched open slowly and gradually, if you could lock yourself in a room for a couple of days just playing with your ass you could probably stretch it enough to fit a dildo the size of an average penis, but if you don't maintain that progress the muscle will snap right back, you're going to need to wear butt plugs for long periods of time and regularly so that the muscle can get used to being stretched open, your skin in that area needs to be able to stretch slowly too.
If you try to force something in there that's too big you risk damaging the muscle tissue, tearing the walls of the anus causing bleeding and increasing the risk of hemorrhoids, so this is a proceed with caution kind of activity.
Butt plug starter kits usually come in various sizes, you're going to need to start with the smallest and build you're way up to the largest, once you're there and comfortable putting it in, taking it out and wearing it for a period of time then you're ready to start getting into rougher strap on pegging with a Mistress and can start thinking about fisting too, though if you want to get into fisting and larger dildos you'll need to invest in some larger butt plugs and dildos and practice by yourself frequently.
If you're not prepared or able to put in the extra time and effort into some training at home then visiting a Mistress once a month/fortnight is not going to get you anywhere, it just isn't frequent enough to keep the anal muscle trained and flexible and every time will be like your first time. You'll never get to the part where you really enjoy it and in session with your Mistress the best you'll ever manage is a 5 minute fingering and maybe 2 minutes of a tiny cock strap on if you're having a good day. Forget the fist, forget the big boys, it ain't gonna happen.
There's nothing wrong with having a little taster and seeing if it's something you can deal with, I get that, but if you really want to fully enjoy anal play it will take some dedication and commitment.
You'll need to learn how to give yourself an enema!
If you are wanting to explore beyond more than a wee little cherry popper cock then you will definitely have to think about hygiene, once you start getting deeper into that cavity it will start getting messy, if you can handle that on your own time then fair play to you, but when it comes to booking a session you will find that many Mistresses require you to perform an anal cleansing before you turn up, it's the polite thing to do. So invest in an enema bulb or purchase a disposable enema kit from the pharmacy.